A chiral synthesis of (-)-spiro[1-azabicyclo[2.2.2] octane-3,5′-oxazolidin-2′-one]:: A conformationally restricted analogue of acetylcholine that is a potent and selective α7 nicotinic receptor agonist

被引：27
|
作者：
Macor, JE [1 ]
Mullen, G [1 ]
Verhoest, P [1 ]
Sampognaro, A [1 ]
Shepardson, B [1 ]
Mack, RA [1 ]
机构：
[1] AstraZeneca, CNS Discovery, Wilmington, DE 19850 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 19期
关键词：
D O I：
10.1021/jo049404q
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A direct, short chiral synthesis of the selective 0 nicotinic receptor agonist (-)-spiro[l-azabicyclo[2.2.2]octane-3,5'-oxazolidin-2'-one] (AR-R17779) is presented. The key step utilized attack of the dianion of the (R)-HYTRA ester [(R)-(+)-2-hydroxy-1,2,2-triphenylethyl acetate] on quinuclidin-3-one, followed by a selective precipitation of the diasteriomeric tertiary alcohol that led to (S)-(-)-AR-R17779 in two additional steps.
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收藏
页码：6493 / 6495
页数：3
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